Diarylsulphone-azodyestuffs



Patented Mar. 14, 1933 OUN'VITED sT'ATas ERNST TIETZE, OF COLOGNE-ON-THE-BHINE, GERMAQNY, ASSIGNOBS TO GENERAL .1; ANILINE WORKS, INC., 01: NEW YORK, N. Y., CORPORATION OF DELAWARE PA EN -OFFICE A WINFRID HENTRIGH, OF ERIIANGEN', ANTON OSSEN'BEGK, COLOGNE- MULH'EIM, AI ND nrmynsunrrroun-nzonyns'rurrs No Drawing. Application filed May 19, 1931, Serial No. 538,628. and a ei aiiy Ma er. 1930.

The present invention relates to new azodyestuffs, more particularly it relates to dyestuifs which may be represented by the probable general formula:

wherein m stands for hydrogen or an alkyl group, y stands for hydrogen or a hydroxy group, 2 stands for hydrogen or alkyl, n stands for one of the numbers one and two, and wherein the benzene nucleus B may be substituted by monovalent substituents, such as halogen, the alkyl-, alkoxy-, hydroxyand carboxylic acid group. V

Our new dyestuffs are obtainable by diazotizing in the usual manner a 2-aminodiaryl-sulphone containing in the aminosubstituted benzene nucleus a sulphainino group, the hydrogen atoms ofwhich maybe substituted by alkyl, said sulphamino group standing in paraposition to the sulphone bridge. and coupling an acid medium with a 2 aminoor alkylaminonaphthalene sulphonic acid or a 2-aminoor alkylamino-S- hydroxynaphthalene-sulphonic acid.

The new dyestufi's are in form of their alkali metal salts generally dark red powders, soluble in water, dyeing wool from an acid bath generally red shades of good fastness properties. The dyestuffs containing in the 2-amino -diarylsulphone-sulphonic acid amide component a hydroxy-' and carboxylic acid group in ortho-position to one another in the benzene nucleus not containing the amino ing.

group are valuable dyestuffsfor after-chrom- As compared with similar known dyestuifs the new sulphone-sulphonicacid amide dyestufisare distinguished particularly by possessing a considerably improved capacity for even dyeing while retaining 'fastness to washing, fulling, perspiration and light.- The'inyention is illustrated" by the followingexamples, without being limited thereto: *Ewamfle 1-386 parts by weightof.

Q-amino-V-hydrQXy diphenyl sulphone 4 sulpho -N monomethylamide 3'-carboxylic acid,'obtainable by the condensationeof sulphino-salicylic acid with 2-nitro-1-chlorobenzene 4- sulpho -'N -monomethy1amide7 (prepared by acting on 1-nitro'-2-chlorobenzene-5- sulphonic acid with phosphorus pentachloride and treating the :su'lphochloride with methylamine) and subsequent'reducti'on, are

diazotized in the customary manner. The diazo compound is coupled in weakly mineral acid solution with 238 "partsby weight of 2-amino-8-hydroxynaphthalene 6 sulphonic acid. When the formation of the dyestuff having in its free state the following formula a V I SOaH is complete, the solution is rendered alka Example 2. 340' parts by .weig ht of 2-.

amino-t'-methyl diphenylsulphone=4esulpho- N-monoethylamide (prepared by condensing in aqueous alcoholic solution ,lchloro 2-ni It dyes w'ool after trobenzene-t-sulpho-N-mono ethylamide with l para-toluene-sulphinic acid and "reducingQQQ v is obtained of properties which are quite 7 product described the nitro group in the usual manner with iron and acetic acid) are diazotized and coupled in acid solution with 237 parts by weight of 2-methylaminon'aphthalene-7-sulphfonic acid. The working up of the dyestuff having in its free state the following formula:

I H 17TH. CH3

sosn

is carried out in the customarymanner.

It dyes wool in an acid bath a vivid red; I the dyeing is very fast to light and fulling and possesses moreover very good evenness.

Dyestuffs of similar properties are obtained by using. as diazo'components 2-a1nino -4: methyl-diphenyl-sulphone4-sulphonamide (prepared by condensing inaqueous alcoholic solution 1-chloro-2 nitrobenzene-4: sulphonamide with para-toluene sulphinic acid and reducing the nitro group in the usual manner with iron and acetic acid), Q-amino-4=chloro=di henylsulphone-4 sulphon-dimethylamide prepared by condensing. in

aqueous alcoholic solution 1-chloro-2-nitrobenzene 4c sulphon-dimethylamide with chloro'-benzene-para-sulphinic acid and reducing the nitro group in the usual manner with iron and acetic acid), and other EZ-amino-diaryl-sulphone-sulphonamides. The 2-methylaminonaphthalene-7-sulphonic acid can a be replaced byother sulphonic acids of 2-aminonaphthalene, for example by the 2-aminonaphthalene-4.7-disulphonic acid. 7

Example 3.When in Example 1 the 'sul phino-salicylic acid is replaced by the sulphino-ortho-cresotinic acid and the process is carried out in a similar manner, a dyestu fl:

having in its free state the following formula:

I oH3 Ho--so2- OzN\ l NH: H coon l analogous to those of the in Example 1; I

Likewise other sulphinic acids, containing the salicylic acid grouping, are suitable for c this purpose.

Example 4.The dyestufi' obtained by acid "coupling 2- aminol hydroxydiphenylsulphone 4 sulphonami do e 3- carboxylic acid,

We claim: V V V 1. The azodyes'tuffsof the'probable'g eral-formula: 1 a j wherein 0: stands for hydrogen or an alkyl I group, 3 stands for hydrogen or a hydroxy group, a stands for hydrogen or analkyl group, n stands for one of the numbers one and two, and wherein the benzene nucleusR may be substituted vloy monovalentsubstitfuents selected from) the group consisting of halogen, an alkyl-,,an a1koxy-, the hydroxyand the carboxylic acid group, being in the form of their alkalijmetal salts generally darkred powders, soluble in water and dyeing wool from anfacid bath generally red shades of good fastness properties;

2. The azody'estuffs oflthe probable general formula:., T, y

v I V ,(s'omm wherein m stands for hydrogen or an alkyl group, y stands for hydrogen-or a hydroxy l.

group, .2 stands for-hydrogen: or an alkyl group,- n stands for "one: of the numbers one and two, and wherein the benzenenucleus .B may contain a hydroxy and Garb oxylic acid group in ortho-position'to one another,as;

substituents, being in the form of their alkali metal salts generally dark red powders, soloble in water and dyeing wool from an aold bath generally red shades of good fastness properties.

3. The azodyestuifs of the probable general formula:

so SOIN H0 OOH wherein :2: stands for hydrogen or alkyl, y stands for hydrogen or a hydroxy group and wherein the hydroxyand carboxylic acid groups in the benzene nucleus R stand in ortho-position to one another, being in the form of their alkali metal salts generally dark red powders, soluble in water and dyeing wool from an acid bath generally red shades of good fastness properties.

mula:

' /OH: HO (Jr-O: OOH IIIHI dyeing Wool after chroming red shades fast to light and fulling and of satisfactory evenness.

5. The azodyestuff of the following for- 0:11 dyeing wool after chroming red shades fast to light and fulling and of satisfactory evenness.

In testimony whereof, We aflix our signatures.

WINFRID HENTRICH. ANTON OSSENBECK. ERNST TIETZE;

4. The axodyestufl's of the following for- 

